Silicone monomers and oligomers having a carboxyl functional group thereon

ABSTRACT

Organosilane and organosiloxane monomers are provided containing at least one carboxyl ester functional group represented by the formula: ##STR1## wherein: R which can be the same or different are hydrolyzable groups; 
     R 1  which can be the same or different, are selected from substituted or unsubstituted alkyl, cycloalkyl, substituted or unsubstituted aryl, alkenyl, alkynyl or --OS i  (R 1 ) 3  ; 
     x is zero to 3; 
     R 2  is linear or branched alkylene of 1-12 carbon atoms; 
     B is --NR 10 , wherein R 10  is hydrogen or a diacarboxylic ester group of the formula--CH 2  --CH(COOR 6 )--CH 2  COOR 6  ; 
     R 5  is hydrogen or alkyl; 
     R 6  is alkyl; 
     F is linear or branched alkylene of 1-10 carbon atoms; 
     R 3  is ##STR2##

RELATED APPLICATIONS

This application is a continuation-in-part of application Ser. No.09/114,100 filed Jul. 13, 1998, U.S. Pat. No. 5,919,938, which was adivision of application Ser. No. 08/911,382 filed Aug. 14, 1997, U.S.Pat. No. 5,780,639.

FIELD OF THE INVENTION

The present invention relates to organosilane and organosiliconecompounds and, more particularly, to novel organosilane compounds andorganosiloxane compounds and oligomers containing a functional carboxylgroup and to a method of making the same.

BACKGROUND OF THE INVENTION

Various organosilane and organosiloxane monomers or compounds includingorganosiloxane oligomers containing one or more organofunctional groupssuch as amines, vinyls, mercaptans, epoxies, halogens, and the like arewidely known. These compounds have been used in a variety of ways suchas coupling agents and adhesion promoters for inorganic materials, asreactants for modifying the properties of organic polymers, ascross-linking agents for curable organic polymer systems, as additivesfor a variety of home care and personal care compositions, as well asmonomers for the preparation of silicon containing polymers.

While silane and siloxane monomers containing a variety oforganofunctional groups are well known and can be readily prepared,organosilane and organosiloxane monomers containing functional carboxylgroups are generally not available commercially. Heretofore, noconvenient method for preparing such monomers with carboxyl functionalgroups has been known and indirect procedures would generally have to beused for their preparation. Accordingly, the development of organosilaneand organosiloxane monomers or compounds containing one or moreorganofunctional carboxyl groups and methods for readily preparing thesecompounds would be desirable, It would be particularly advantageous ifmethods for preparing such compounds not only employed readily availablematerials, but carboxyl-functional organosilicone monomers and oligomerscould be prepared containing other functional groups as well, such ashalogen groups, which makes possible the preparation of a variety oforganosilicone derivatives including oligomers thereof.

While, as indicated, organosilane and organosiloxane compoundscontaining a variety of functional groups and methods for preparing thesame, heretofore, have been known and used, there is no known disclosureor suggestion of the novel carboxyl-functional organosilane andorganosiloxane compounds and oligomers of the present invention or ofthe method for making the same herein described.

SUMMARY OF THE INVENTION

It is accordingly an object of the present invention to provide a novelclass of organosilane and organosiloxane compounds having at least onefunctional carboxylic ester group thereon and which may also include avariety of other functional groups as well.

It is another object of the present invention to provide a novel classof organosilane and organosiloxane compounds having at least onepyrrolidone-containing carboxylic ester and/or acid functional groupsthereon including an amphoteric class of organosilane and organosiloxanecompounds which may also include other functional groups as well.

It is yet another object of the present invention to provide a novelclass of organosiloxane compounds and oligomers having at least onefunctional carboxylic ester and/or acid group thereon.

It is a further object of the present invention to provide a process forreadily producing organosilane and organosiloxane compounds containingat least one carboxylic ester functional group.

These and other objects will become apparent from the dscription tofollow.

In accordance with the present invention, there has now been discoverednovel organosilane and organosiloxane compounds containing one or morefunctional carboxylic ester group(s) that may be represented by thefollowing general formula: ##STR3## wherein: R, which can be the same ordifferent, are hydrolyzable groups such as but not limited to halogen,acyloxy, N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio, cyano or alkoxy;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkenyl,alkynyl or --O--Si--(R¹)₃ ;

x can be zero to 3;

R² is linear or branched alkylene of 1-12 carbon atoms, preferablymethylene;

R⁵ is hydrogen or alkyl (C₁₋₁₀);

B is --NR¹⁰, wherein R¹⁰ is a dicarboxylic ester group of the formula--CH₂ --CH(COOR⁶)--CH₂ COOR⁶ ;

R⁶ is alkyl (C₁₋₂₀) or trialkylsilyl;

F is linear or branched alkylene of 1-10 carbon atoms, preferablyethylene;

R³ is ##STR4##

In another aspect of the present invention there are provided novelorganosiloxane compounds and oligomers containing one or more functionalcarboxylic ester groups that may be represented by the formula: ##STR5##wherein: R which can be the same or different, are hydrolyzable groupssuch as but not limited to halogen, hydroxy, alkoxy, alkoxyalkoxy,acyloxy, N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ are as hereinabove defined;

R⁷ and R⁸, which may be the same or different, are selected from alkyl,aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenylor alkynyl;

M can be the same or different and is selected from hydrogen, R, R¹ and--CH₂ --CHR⁵ --R² --B--F--R³, with the proviso that at least one M is--CH₂ --CHR⁵ --R² --B--F--R³ ;

y can be zero to 2;

a is from zero to 10;

b is from zero to 10;

R², R³, R⁵, R⁶, B and F are as defined hereinabove.

In yet another aspect of the present invention there is provided amethod for preparing organosilane or organosiloxane monomers containingone or more pyrrolidone-containing functional carboxyl ester groupswhich comprises reacting a N-alkenyl pyrrolidone containing acarboalkoxyl group of the formula

    CH.sub.2 ═CR.sup.5 --R--B--F--R.sup.3

wherein:

R², R³, R⁵, R⁶, F and B are as hereinabove defined. with an organosilanehydride having one or more hydride groups of the formula ##STR6##wherein: R, which can be the same or different, are hydrolyzable groupssuch as but not limited to halogen, alkoxy, alkoxyalkoxy, acyloxy,N,N-Dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ and x are as hereinabove defined;

at an elevated temperature (preferably between 65° C. and 130° C.) inthe presence of a noble metal catalyst for a time sufficient to reactthe hydride group(s) on the silicon atom with the olefinic group on thepyrrolidone.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

In accordance with the present invention there are provided novelorganosilane and organosiloxane monomers or compounds containing acarboxylic ester functional group which may be represented by thegeneral formula: ##STR7## wherein: R which can be the same or different,are hydrolyzable groups such as but not limited to halogen, acyloxy,N,N-Dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio, cyano or alkoxy;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, preferably lower alkyl (C₁ -C₆); cycloalkyl, e.g. cycloheptyl;aralkyl, e.g. benzyl, phenylethyl etc.; substituted or unsubstitutedaryl; alkenyl; alkynyl or --OSi(R¹)₃ ;

x can be zero to 3;

R² is linear or branched alkylene of 1-12 carbon atoms, preferablymethylene;

R⁵ is hydrogen or alkyl C₁₋₁₀) preferably methyl;

B is --NR¹⁰, wherein R¹⁰ is hydrogen or a dicarboxylic ester group ofthe formula --CH₂ --CH(COOR⁶)--CH₂ COOR⁶ ;

R⁶ is alkyl (C₁₋₂₀) or trialkylsilyl;

F is linear or branched alkylene of 1-10 carbon atoms, preferablyethylene;

R³ is ##STR8##

In accordance with the present invention there are also providedorganosiloxane compounds and oligomers containing one or more functionalcarboxyl groups that may be represented by the formula: ##STR9##wherein: R, which can be the same or different, are hydrolyzable groupssuch as but not limited to halogen, hydroxy, alkoxy, alkoxyalkoxy,acyloxy, N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkenyl,alkynyl or --O--Si--(R¹)₃ ;

R⁷ and R⁸, which may be the same or different, are selected from alkyl,aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenylor alkynyl;

M can be the same or different and is selected from hydrogen, R, R¹ and--CH₂ --CHR⁵ --R² --B--F--R³, with the proviso that at least one M groupis --CH₂ --CHR⁵ --R² --B--F--R³ ;

y can be zero to 2;

a is from zero to 10;

b is from zero to 10;

R², R³, R⁵, R⁶, B and F are as defined hereinabove.

The novel carboxylic ester functional organosilane and organosiloxanemonomers of the present invention surprisingly and unexpectedly can bereadily prepared by reacting a silane monomer having one or more hydridesubstituents on the silicon atom of the formula: ##STR10## with apyrrolidone nucleus containing a N-monosubstituted terminal olefinicgroup of the formula:

    CH.sub.2 ═CR.sup.5 --R.sup.2 --B--F--R.sup.3

wherein:

R which can be the same or different, are hydrolyzable groups such asbut not limited to halogen, alkoxy, alkoxyalkoxy, acyloxy,N,N-Dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, preferably lower alkyl (C₁ -C₆); cycloalkyl, e.g. cycloheptyl;aralkyl, e.g. benzyl, phenylethyl etc.; substituted or unsubstitutedaryl; alkenyl; alkynyl or --OSi(R¹)₃ ;

x can be zero to 3;

R² is linear or branched alkylene of 1-12 carbon atoms, preferablymethylene;

B is --NR¹⁰, wherein R¹⁰ is a dicarboxylic ester group of the formula--CH₂ --CH(COOR⁶)--CH₂ COOR⁶ ;

R⁵ is H or alkyl (C₁₋₂₀); preferably hydrogen or methyl;

R⁶ is alkyl (C₁₋₂₀) or trialkylsilyl;

F is linear or branched alkylene of 1-10 carbon atoms, preferablyethylene;

R³ is ##STR11##

The reaction is carried out in the presence of a noble metal (Group VIIImetal) catalyst, preferably soluble platinum, at an elevated temperature(65° C. to 130° C.) for a time sufficient for substantially all of theN-alkenyl carboalkoxy containing molecule to react with the hydridegroup(s).

The reaction can be carried out neat or in inert solvents such astoluene, benzene, chlorobenzene, heptane and the like. In general, fromabout 0.5, preferably from about 0.9 to 1.1 equivalents of the N-alkenylcarboalkoxy containing molecule groups per functional hydride groups isreacted with the hydride groups of the silane monomer, whereinsubstantially all the N-alkenyl carboalkoxy containing molecule and,preferably all of the functional hydride group(s) are reacted and anorganosilane or organosiloxane compound with at least onepyrrolidone-containing functional-carboxylic ester group(s) togetherwith a substitute aminomethyl succinic acid ester derivative, is formed.The reaction is carried out in the presence of a noble metal catalyst.Suitable platinum catalysts include solubilized platinum or platinummetal on supports such as alumina, charcoal and the like. In generalfrom about 10⁻³ to 10⁻⁶ moles of platinum per mole of hydride group canbe used.

The carboalkoxy containing pyrrolidone reactant suitable for use inaccordance with the practice of the present invention may be prepared bythe reaction of an olefinic diamine having a functional primary aminegroup(s) of the formula: ##STR12## wherein: R² is linear or branchedalkylene of 1-12 carbon atoms, preferably methylene;

R⁵ is hydrogen or alkyl (C₁₋₂₀), preferably hydrogen or methyl;

R⁶ is alkyl (C₁₋₂₀) or trialkylsilyl; and

F is linear or branched alkylene 1-10 carbon atoms, preferably ethylene;

with up to about two equivalents of itaconic ester per olefin group atan elevated temperature for a time sufficient for substantially all ofthe itaconic ester to react with the primary and secondary aminegroup(s) and the formation of pyrrolidone containing a carboalkoxylfunctional group(s).

Itaconic acid (methylene succinic acid) ester is a compound of theformula:

    CH.sub.2 ═C(COOR.sup.6)--CH.sub.2 --COOR.sup.6

wherein

R⁶, which can be the same or different, is alkyl (C₁₋₂₀) ortrialkylsilyl preferably lower alkyl (1-6 carbon atoms).

The compound itaconic acid is available commercially from PfizerChemicals Division and Rhone Poulenc whereas ester derivatives thereofare available from Morflex, Inc., Greensboro, N.C. The compounds areproduced by known fermentation techniques although chemical synthesismethods are also known.

Olefinic diamine compounds suitable for use are any olefinic diamineshaving at least one primary amine group of the formula: ##STR13##wherein, R², R⁵, B and F are as hereinabove defined.

Exemplary suitable allyl diamine compounds are N-allyl ethylene diamine,N-allyl propylene diamine and N-allyl--N-methyl propylene diamine.

In general, from about 1.25, preferably from about 1.9 to about 2.1,equivalents of itaconic ester per functional primary and secondary aminegroup is reacted with the primary and secondary amine group of theolefinic amine compound wherein substantially all of the itaconic andpreferably all the primary and secondary amine group(s) are reacted andan N-alkenyl carboalkoxy compound containing a pyrrolidone nucleus isformed of the formula:

    CH.sub.2 ═CR.sup.5 --R.sup.2 --B--F--R.sup.3

wherein

R², R⁵, B, F and R³ are as defined hereinabove.

The reaction can be carried out neat or in an inert solvent such asalcohol, hydrocarbon solvent, chlorinated hydrocarbon and the like, asdesired, in general at elevated temperatures up to about 175° C.,preferably from about 90° C. to about 130° C. The reaction readilyproceeds and generally complete reaction of the itaconic ester with theavailable primary and secondary amine group(s) occurs in the MichaelAddition manner with the double bond of the itaconic ester followed byimmediate cyclization of the primary amine hydrogen with by additiveadduct to form a pyrrolidone group which will occur in from about 1 to 5hours.

In another aspect of the present invention, the novel organosiloxanecompounds and oligomers of the present invention can be readily preparedby reacting an organosiloxane compound or oligomer having one or morehydride groups on the silicone atoms of the formula: ##STR14## wherein:R, which can be the same or different, are hydrolyzable groups such asbut not limited to halogen, alkoxy, alkoxyalkoxy, acyloxy,N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkenyl,alkynyl or --O--Si--(R¹)₃

R⁷ and R⁸, which may be the same or different, are selected from alkyl,aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenylor alkynyl;

N can be the same or different and is selected from hydrogen, R and R¹,with the proviso that at least one N group is hydrogen;

y can be zero to 2;

a is from zero to 10;

b is from zero to 10;

With an N-alkenyl carboalkoxy compound containing a pyrrolidone nucleusof the formula CH₂ ═CR⁵ --R² --B--F--R³ as hereinabove described,preferably with one olefin per hydride group. The reaction is carriedout as hereinabove described in the presence of a noble metal (GroupVIII metal) catalyst, preferably soluble platinum, at an elevatedtemperature (65° to 130° C.) for a time sufficient for substantially allof the N-alkenylcarboalkoxy containing pyrrolidone to react with thehydride group(s).

The organosilicone monomers according to the present invention areuseful, for example, as coupling agents and adhesion promoters forinorganic materials, as reactants for modifying the properties oforganic polymers, as crosslinking agents for curable organic polymers,as additives for personal and home care products, as precursors fororganic or organosilicone polymers of varying molecular weights and thelike.

The above is a general description of the present invention. Thefollowing examples are given for the purpose of illustration and are notintended in any way to limit the invention as claimed. Unless noted tothe contrary, proportions are on a weight basis.

EXAMPLE 1

This example illustrates the method for making N-allyl-4-carbomethoxypyrrolidone.

A solution of 158 grams of Dimethyl itaconate and 200 ml of methanol ischarged to a reaction vessel and 57 grams of allyl amine is addeddropwise to the itaconate solution with agitation in the reactionvessel. During addition of allyl amine to the reaction mixture, thetemperature increased from ambient to 62° C.

Upon complete addition of the allyl amine the reaction mixture is keptat reflux for 4 additional hours. The methanol is distilled from thereaction mixture and the reaction product is distilled at 115° C. underreduced pressure (1 mm). A yield of 92% is obtained. The structure ofthe reaction product is evaluated by IR.

EXAMPLE 2

This example illustrates the preparation of N-(Dimethylchlorosilylpropyl)-4-carbomethoxy pyrrolidone.

To 183 grams of N-allyl-4-carbomethoxy pyrrolidone prepared as describedin Example 1 and 1 ml of 0.1 N-chloroplatinic acid in isopropanolcharged to a reaction vessel with agitation, 94.5 grams of Dimethylchlorosilane is added dropwise to the reaction mixture and an exothermoccurs increasing the reaction mixture temperature to 90-95° C. Thereaction temperature is maintained at 95° C. for 4 hours after all thesilane reactant is added to the reaction mixture. A colorless oil isobtained by distilling at 168-170° C. under 2 mm pressure with about 90%yield. The structure of the reaction product is confirmed by NMR and IR.

EXAMPLE 3

This example illustrates the preparation ofN-(Dichloromethylsilypropyl)-4-Carbomethoxy pyrrolidone.

A reaction mixture of 183 grams of N-allyl-4-carbomethoxy pyrrolidoneprepared as described in Example 1 and 1 ml of 0.1N chloroplatinic acidin isopropanol is charged to a reaction vessel. 115 grams ofmethyldichlorosilane is added dropwise to the reaction mixture withagitation during which an exothermic reaction occurs increasing thetemperature of the reaction mixture to 90-95° C. The temperature of thereaction mixture is maintained at 95° C. for 4 hours after the additionof the silane is completed. The reaction mixture is distilled duringwhich a colorless oil is obtained at a temperature of 174-176° C. under2 mm pressure. A yield of product of 93% is obtained and the structureis confirmed by IR and NMR.

EXAMPLE 4

This example illustrates the preparation ofN-(Triacetoxysilylpropyl)-4-carbomethoxy pyrrolidone.

A reaction mixture is prepared from 183 grams of N-allyl-4-carbomethoxyprepared as described in example 1 and 1 ml of 0.1 N chloroplatinic acidin a reaction vessel. 206 grams of triacetoxysilane is added dropwise tothe reaction during which an exotherm is created increasing the reactionmixture to 110-115° C. After all the silane reactant has been added, thetemperature of the reaction mixture is maintained at 110° C. for 3hours. A low melting reaction product is recovered from the solidreaction vessel and the structure of the product is confirmed by NMR andIR.

EXAMPLE 5

This example illustrates the preparation of N-[Bis(methylethylketoximino) methylsilylpropyl]-4-carbomethoxy pyrrolidone.

A reaction mixture is charged to a reaction vessel containing equalmolar amounts of Bis(methyl ethyl ketoximino) methyl silane andN-allyl-4-carbomethoxy pyrrolidone and about 10⁻⁴ moles ofchloroplatinic acid in isopropanol. The reaction mixture forms anexotherm of about 110° C. after which the reaction mixture is maintainedat 130° C. for 3 hours. The structure of the reaction product isconfirmed by NMR and IR.

EXAMPLE 6

This example illustrates the preparation of N-(Trichlorosilylpropyloxypropyl)-4-carbomethoxy pyrrolidone.

A reaction mixture of 236 grams of N-allyloxypropyl-4-carbomethoxypyrrolidone prepared by replacing allyl amine with allyloxypropyl amineas described in Example 1. 0.1 N chloroplatinic acid and isopropanol ischarged to a reaction vessel and heated to about 85° C. 135.5 grams ofTrichlorosilane is added dropwise to the reaction mixture withagitation. The reaction mixture is exothermic and heat is removed tomaintain the temperature at about 90-95° C. Upon adding all thetrichlorosilane, the reaction temperature is maintained at 120°C. for 2hours. Low boiling is materials are stripped from the reaction mixtureunder reduced pressure. A yield of 95% of product is obtained and thestructure of the reaction product is confirmed by I.R. and NMR.

EXAMPLE 7

The addition of methyldichlorosilane toN-(allylthiopropyl)-4-carbomethoxy pyrrolidone in the presence ofcatalytic amounts of chloroplatinic acid results in the formation ofN-(methyldichlorosilylpropylthiopropyl)-4-carbomethoxy pyrrolidone withyields and structure confirmed by G.C. analysis, I.R. and NMR.

EXAMPLE 8

Allyl methyl amine is cyanoethylated with acrylonitrile followed bypalladium catalyzed reaction with hydrogen to prepare the reactionproduct N-allyl, N-methyl, propylene diamine is identified by NMR andI.R.

Equimolar amounts of N-allyl, N-methyl, propylene diamine prepared asdescribed above and Dimethyl Itaconate are charged to a reaction vesseland heated slowly with agitation to 130°-150° C. After the exothermsubsides, the reaction mixture is maintained at 140° C. for 3 hours. Thereaction product 1-(N-allyl, N-methyl aminopropyl)-4-carbomethoxypyrrolidone is isolated by distillation.

Triethoxysilane is added dropwise to an equimolar amount of the1-(N-allyl, N-methyl aminopropyl)-4-Carbomethxyl pyrrolidone preparedabove in the presence of 0.1M chloroplatinic acid while maintaining areaction temperature of 120°-140° C. After completion of the reaction,the product is isolated by fractionation of the reaction mixture and theproduct is identified by NMR and I.R.

EXAMPLE 9

This example illustrates the preparation of methyl N-(N¹ trimethoxysilylpropyl, N¹ -Dimethyl succinato methylene) aminoethyl 4-pyrrolidonecorboxylate.

A mixture of 10 grams of N-allylethylene diamine and 316 grams ofdimethyl itaconate is heated to 95-110° C. for six hours. Upon cooling,low boiling components are removed by heating the mixture at 75-100° C.at 10 mm for 2 hours.

Equimolar amounts of trimethoxy silane is added with mixing to the abovereaction product in the presence of 10⁻⁴ moles of chhloro-platinic acidper mole of silane. The reaction product is methyl N-(N¹ trimethoxysilylpropyl, N¹ -Dimethyl succinato methylene) aminoethyl 4-pyrrolidonecorboxylate.

What is claimed is:
 1. Organosilane and organosiloxane monomers havingat least one carboxylic ester functional group represented by theformula: ##STR15## wherein: R which are the same or differenthydrolyzable groups;R¹ which are the same or different groups, selectedfrom substituted or unsubstituted alkyl, cycloalkyl, substituted orunsubstituted aryl, alkenyl, alkynyl or --OS_(i) (R¹)₃ ; x is zero to 3;R² is linear or branched alkylene of 1-12 carbon atoms; R⁵ is hydrogenor alkyl; B is --NR¹⁰, wherein R¹⁰ is a dicarboxylic ester group of theformula CH₂ --CH(COOR⁶)--CH₂ COOR⁶ ; R⁶ is alkyl or trialkylsilyl; F islinear or branched alkylene of 1-10 carbon atoms; R³ is ##STR16##
 2. Theorganosilane and organosiloxane monomers as claimed in claim 1, whereinR are hydrolyzable groups selected from halogen, acyloxy,N,N-Dialkyl-aminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio, cyano, alkoxy and alkoxyalkoxy groups.
 3. Theorganosilane and organosiloxane monomers as claimed in claim 2, whereinR¹ is selected from substituted or unsubstituted lower alkyl,cycloalkyl, substituted or unsubstituted aryl, alkenyl, alkynyl or--OS_(i) (R¹)₃.
 4. The organosilane and organosiloxane monomers asclaimed in claim 2, wherein R⁶ is lower alkyl.
 5. The organosilane andorganosiloxane monomers as claimed in claim 2, wherein said compoundsare an amphoteric class of organosilicone compounds and R¹ is selectedfrom substituted or unsubstituted alkyl, substituted or unsubstitutedaryl, alkenyl, alkynyl or --OS_(i) (R¹)₃.
 6. The organosilane andorganosiloxane monomers as claimed in claim 1, wherein R¹ is --OS_(i)(CH₃)₃ and x is 1 to
 3. 7. The organosilane and organosiloxane monomersas claimed in claim 6, wherein R² is methylene, R⁵ is hydrogen ormethyl.
 8. The method of preparing organosiloxane compounds containingone or more pyrrolidone groups having functional carboxyl ester groupswhich comprises reacting a N-alkenyl pyrrolidone containing acarboalkoxyl group of the formula:

    CH.sub.2 ═CR.sup.5 --R.sup.2 --B--F--R.sup.3

wherein: R² is a linear or branched alkylene of 1-12 carbon atoms; R⁵ ishydrogen or alkyl; R⁶ is alkyl; F is linear or branched alkylene of 1-10carbon atoms; B is --NR¹⁰ ; R¹⁰ is a dicarboxylic ester group of theformula--CH₂ --CH(COOR⁶)--CH₂ COOR⁶ ; R³ is ##STR17## with anorganosilane hydride group of the formula: ##STR18## wherein: R isselected from a hydrolyzable group;R¹ is selected from substituted orunsubstituted alkyl, cycloalkyl, substituted or unsubstituted aryl,aralkyl, alkeneyl, alkynyl or --O--Si--(R¹)₃ groups or mixtures of thesame; x is from 0 to 3;at an elevated temperature in the presence of anoble metal catalyst for a time sufficient to react the hydride groupson the silicone atom with an olefinic group on the pyrrolidone.
 9. Themethod of preparing organosiloxane compounds as claimed in claim 8,wherein R are the same or different hydrolyzable groups selected fromhalogen, alkoxy, alkoxyalkoxy acyloxy, N,N-Dialkylamoxy, N-alkylamido,monoalkylamino, dialkylamino, isocyanato, alkylthio, or cyano groups ormixtures of the same.